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Rebuilding Asana’s Brand, Narrative, and GTM, with Prachi Gore (the CMO Who Grew Checkr to $800M)

52m 51s

Rebuilding Asana’s Brand, Narrative, and GTM, with Prachi Gore (the CMO Who Grew Checkr to $800M)

This episode highlights how AI is transforming B2B marketing, from automating workflows to redefining product positioning. Mcheal from Optimizedly demonstrates the power of AI agents in ABM by building thousands of custom landing pages from real-world signals, validating AI’s potential for targeted marketing. Optimizedly’s platform empowers marketers with AI agents that can join meetings, manage campaigns, and maintain websites—making AI a core part of daily operations. Similarly, Webflow enables brands to leverage AI for content creation and campaign automation, turning websites into ongoing revenue engines. The conversation with Prachi Gauray, CMO at Asana, reveals how a strategic repositioning—without external agencies—was achieved through internal alignment, clear decision-making frameworks, and CEO involvement. Asana shifted from project management to work execution by integrating AI agents into workflows, enabling teams to collaborate more efficiently and build shared memory across functions. Five new products were launched in six months, using a high-impact event as a launch moment and building campaigns around specific use cases. The marketing team is structured with clear KPIs and cadences, emphasizing collaboration between demand, growth, and revenue marketing. Ultimately, the episode underscores that while AI enhances efficiency, human creativity, strategic leadership, and real-world experience remain essential—proving that the future of marketing lies in human-AI synergy, not automation alone.

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Dasha, remember when Mcheal from Optimizedly won our exit five live AI agent showcase the 2000 custom landing pages. That was really impressive So he's their director of AI innovation and he built them with Optimizedly's agent platform won for every account in an ABM campaign He built them from signals like job postings, press releases and leadership changes. That's like the holy grail of ABM That's why today's sponsor Optimizedly is where I'd point anyone who wants to know what AI agents can do for marketing Their agent platform is built specifically for B2B marketers build your own agents or pull from a directory of 50+ prebuilt ones They also launch virtual teammates these are digital team members that learn over time can join meetings complete tasks support campaigns and keep your website Optimized, why do I need to go to work? Let me get those. Okay, I need one of those Same being asked to look into AI agents, which I know a lot of you listeners are right now go check out Optimizedly Put them at the top of your list and you can go build cool stuff just like Mcheal did check them out at Optimizedly.com/exit5 Hey quick shout out to web flow who is also sponsoring today's episode their team actually ran one of the highest rated workshops at Drive this year Which is our big annual conference people raved about that one guy their chief evangelist really knows aio And you shared a ton of advice on turning your website into an ongoing revenue driver And that matters a lot right now right AI is cutting into organic traffic. I don't go to Google and search anymore I'm talking to my AI agents all day long So AI is cutting into organic traffic and buyers just like you and me are using AI to make purchase decisions about 95% of the time Web flow they're a great team to follow on this more than 300,000 brands can you believe that build on their platform And helps you get discovered in AI search build fully custom sites without a developer govern your content and see how agents read it all in one place and they just launched web flow campaigns agents help you write a campaign brief from your brand system then generate on brand landing pages and matching ads together check it out at webflow.com/exit-5 And make your website your biggest growth engine in 2027 that's webflow.com/exit-5 You're listening to the exit-5 podcast Hey my guest on this episode is Pratchee Gauray. She is the CMO at Asana And within about six months of joining she did five new product launches Let a new brand new corporate narrative and positioning And unveiled a new Asana work innovation summit before that She spent six years at checker where the business grew from over a hundred million in revenue to 800 while she was there At checker she had this PLG self-serve business and an enterprise business And now they have a similar motion at Asana. I know a lot of people that listen to our podcasts have that motion So we talked a lot about that. What is her team structure? What are the marketers at Asana do? What are her big priorities for the year? How does she have the team structured and organized and where does she think things are going? Because of all the AI stuff that's happening in this world and also we tell the story about how they actually did the Asana repositioning exercise and why she chose to not work with an agency or consultant Why they did it all in house and what they learned through that. This is a really awesome conversation with The CMO of a product. I know a lot of you are using and love and just an interesting insight into High-performing marketing team and what they're doing right now. Enjoy my conversation with Pratchee from Asana Shout out to Asana Our team is our power users Marissa, she can't get me to log in so maybe that's a product marketing thing later I'm more of a - you'll fix that. I need to see why not. I'm more of a posted note guy myself, but Yeah, okay. We have notes, you know, in Asana, but By the end of this call I will be I will be a power user, but uh excited to to have you on the pod You know, obviously we our audiences B2B marketers. I'm sure there's lots of Asana power users out there You are relatively new. Is it is in the last year? Yeah Okay, what note on the worst it is coming up soon. So yes Okay, before this before this you were running marketing at checker. Yes. I was there for six years What's the difference between what you were doing at checker and with the audience that you're going after At Asana and tell people who checker like who you sold to at checker what you kind of just that ICP and then what you're doing now And I'm also curious as to like why Asana you're having an impressive resume. Why'd you why'd you take that job? Why'd you go there? Yeah I'll share all of it So checkered started on as a background checks window and so in our early days and I was there six years So I joined when we were a four-year-old company and then the business grew But in our early days our target audience was developers because we had APIs And so all these good companies and marketplaces wanted to use the APIs and and into background checks as part of their Occasion process for drivers, etc. And then we grew to like sort of the larger each our audience So background checks for everyone and then maybe halfway like through my tenure there We went from single product to multi product company and started building all these other trust and compliance products for insurance agencies for marketplaces for So the breadth of our audience is grew as our product grew but our The largest part of our revenue still comes from what I categorize as each our audiences. So that's checkered Asana is very different Asana is a product that anyone can use. It's a hard example product So technically anyone who wants to manage projects We have people who manage their weddings through Asana and all the way to you know large large fortune and hundred companies Marissa's gonna listen this later because she's our content person and she's goes and listens I I didn't know Marissa when she got married, but if I had to guess Asana was heavily involved in her. Yeah, for sure Yeah, so we have that. It's like one of the use cases But we sort of everyone however, I'm a big fan of ICP so within the universe of anyone can use Asana we go after I wouldn't say like ops audiences, but like marketing marketing ops campaign ops creative ops as well as like strategic ops program management offices So it's like marketing and ops as audiences out our print the audiences It's interesting to hear you said it because I through running x5 right we talked to lots of different marketing people in all different industries and Sometimes you talk to a company where it's like anyone can use our product and to some people whoever really small like ICP You're like wow, that's amazing, but it can be a challenge because it's like how do you do marketing to everyone? How do you make the website speak to all these people and it's not just external you have All these stakeholders internally who run different parts and they're like we're battling with the sales over this segment or this product person wants more voice And so it's interesting to hear that like anyone can buy Asana, but from a who you're actively marketing to your focus is that the right way to read that exactly I think what the ICP does is like it creates almost within your resourcing and investment decisions of prioritization framework Or even like plays that we work with our sales team. It's like hey notice on each one Please like let's go after these target ICPs and sometimes that's what because sometimes that's for so now But you got to like figure out where do you have the highest propensity to win Even if you are a hot example fairly hot example product I have a bunch of questions that I want to ask you in our doc and I I like to our audiences all marketing nerds right like kind of like you and me They like to hear about how do you have the team structured? How does Prachi run the marketing team? I want to get into some of this stuff you've done in Asana what won't get there, but I'm just curious What is the first year of your job in like and you've been a marketing leader in the past and so you've had an opportunity to you know This is not the first time you've joined a company as a marketing leader What do you come in and do how do you know the right time to make changes? Take me into the first year at Asana and how you've and one more thing and I'll shut up everyone says like Don't come in and do a rebrand don't come in and all that There's so much nuance to all that it's different in every company I want to hear like what what have you done? What if you come in and evaluate it and change or moved around or kept right? I'll tell you what I've done at Asana and then I do want to comment on like the rebrand aspect especially when you go into a new job But as a marketing leader so when I came to Asana There were two jobs to be done or like key objectives for me and my marketing team one was Asana was going from a collaborative work management product or project management product To becoming work execution because the beauty of that collaboration that happened between humans and humans was that when you introduce agents into Teams and let's call them hybrid teams The agents also need to collaborate with the humans or the agents themselves So the collaboration aspect doesn't go away. It is needed What is especially in a multi-player way like if I I have a brand strategist and both of us want to work without with my brand Straightening just agent then we need a collaboration problem what Was amazing about this is that now that we have agents in the system work can actually get executed and we could talk more about like what kind of work But but that's very different from being a project management system Now you're like moving towards a work execution system So the brand being or I would say it wasn't even like visual branding wasn't The first step but the positioning repositioning of who is Asana needed to happen So you're saying like the Asana product strategy change because it's like wait Dave's got a bunch of things on his to-do list that like an agent could just do and not just that because it's like you could say okay I could be like in an LLM agent or plot or whatever and and that can happen too but where the power was is like oh Prachi okay I'll give you an example the the one that comes up is one of the most standard ones in any marketing field I need to update the website create a new lending page for my campaign whatever the old process would have been me the marketer would have created if you're a big org like a ticket or something or I would have gone and talked to someone in web to say like I need to lodge this new page I then you bring in a designer you bring in a content writer if you're a scale team and if you're small and you have all these people playing and before you even write something you've had a kickoff call you've had like action items you've like done this for process in the agents in our system process the marketer is still saying hey I need to here's we have a meetings product too that's like that LGA now in a month but we use it so we have done this kickoff meeting the marketer saying I want to go do this the meeting is recorded it's an agent it's taking the transcript creating the action plan of what needs to happen we have pre-built agents like the creative pre-frider launch planner but the in this case the creative pre-frider saying okay great I got this I'm going to write the creative brief based on on this and suggested copy then it goes we have we always have human in the loop so someone saying like this copy is fine or not fine or whatever it's usually not fine so they're like give some prompting but you know it's like do stand out like for some like SEO type of stuff it's usually fine yeah well I think yeah no it's fine you don't have to couch I think it's it's definitely helpful from going from zero to one I like having the human in the loop it's like hey like let's give it the right feedback but the beauty of this agent is like let's say that copy came to you and me we are like I'm the web team you're the content editor and we are both giving it feedback me for SEO or something and you're giving it for like tone or just like creativity or just like not having a POV or something this brand strategy just now has executed on that feedback but now it's created memory from both what I told it as well as what Dave told it and so this is like shared memory and so it's like literally like a real teammate like I have a brand strategy just stream it that multiple people have coached and which is different from your agent in an LLM so I think that's the the power that gives our teams is like we are thinking about these workflows and to end and say okay one of the steps that agents can do where do I want the human and it can be a large part can be automated like this web example our team was saying like they saved somewhere between 11 to 15 hours every week that they would have spent doing something you know around this so your job then I'm just like checking out the website right now so your job as a marketing leader did this story exist before you got there did you need to come in and like basically talk about the new Asana to the world we have to talk about the new Asana what existed was this idea that we were going to become agent we had relaunched like some agents but if nothing was GA the story wasn't like flushed and it was not about the workflow it was about the agents but it's not about the agents the agents there are many every product is going to have them and are going to get commoditized you need them but largely there are many types of agents so it was like the differentiation of our agents which needs to stand out but really the move was towards orchestrated execution it's like moving from tracking to orchestration so that had to happen when I came and this like all of it's all about the workflow which we get talk about through our process as we were uncovering what is that position but yeah so that was like one it's like we got a reposition or something yeah let I have that later let we'll get there I want to talk about the position yes yeah so we that was one and then two was we we have to bring growth back like the company is growing this is publicly available data but we are growing like in that 10% range how do we get to 20 how do we bring like inflective growth back and so those were the two world are but like when I first came in those were the two objectives for the marketing leader and so then I had to like take a step back and say okay how are we going to organize ourselves to go to this and we have to launch five new products by June so it was like I was like I was telling someone jokingly my first six months I was like I didn't think I was going to join your like reposition the company we did end up doing a visual rebrand and launch five new products and a flagship rebrand all in six months so it was crazy times what fun and then I want to go back to the branding I do firmly believe that you shouldn't just go in as a new CMO and like rebrand you should if something is categorically not working or is fundamentally changing that will drive the objective that you have been brought into drive and that's growth or whatever and sometimes because it's rebranding for the sake of rebranding is such a costly project not just like dollar wise with the amount of effort and team effort you're putting in it's like expensive and so if I ever have the choice and if the current brand was working I wouldn't like it would be the last I love doing branding I love ring positioning it's fun but I would not I would not try and touch it first if it didn't have a touch anything is like one of those things that people love to just like debate about on LinkedIn but I think there's just so much nuance to it obviously if you went to a company and it was like so obvious that the brand didn't represent what the company was actually doing then that actually could be a lever I think that's crazy by the way five five new products in six months I'm just like typing some of these things as you say them so I can come back to them I'm not ignoring you five new products in six months and a whole rebrand how did you do that how did you do that why didn't you push back why didn't you say no and I'm saying that because I got a text from one of our members over the weekend and she was like I just took this new job am I crazy they want this this this this this in the first 90 days now that 90 days not six months but take me through that how do you actually decide to go do that how do you block and tackle it how do you you have a new team who doesn't know who you are yet or doesn't know your working style like there's a lot in there it is and it's not is not and was not easy on anyone so it was a lot of like fun but also sweat and tears and learnings I would say you asked the question why did you not push back the need to go tell the Asana story to go drive the growth the inflective growth was needed like it was necessary we our core market is growing at the rate it's growing but we could deliver so much more value to our customers we had to go tell that story the five product launches came a little bit later and and they came because our edge teams productivity just skyrocketed with the innovation of coding tools and so a timeline when I first got in here late last year the timeline was more spread out through the year and we have like two big events that we do but our teams were just able to deliver this amazing innovation and so it didn't make sense to hold that back and not announce it so we pulled it forward and announced these products however we did stagger the EAGA launches so that we can do the due diligence on enabling our teams in detail like you know having the plays and the campaigns ready so the big external push and the GAs EAGAs we did stagger but the announcement we had to go make because the products were gone up ready or were ready this is going to happen if this is going to continue to happen like we were having this discussion at our product launches and I've been around the block a lot we used to do like these batch batch releases and product launches another one which is like yeah batched product releases then we went to like hey we could why wait like we just like do you know the last three or five years were just like oh go go like push your innovation and right now I see this day I don't know that we've decided that but I am as I think about next year like I'm like our teams are just launching something new every week it's like does it make sense to go back to batch to just like give our customers the moment to absorb what is happening and so this is kind of where I was going with this is like what can you take me into what some of those product launches even are what's the playbook because yeah you're I my one of my first jobs in marketing was like writing release notes and it would be like once a quarter like there'd be a bunch of new products product updates and I would write them and be a blog post and an email you're a sauna publicly traded company lots of people know you are you on stage but also like do people care at that level like can you tell me like what when you say like we launch the five products what were the marketing components of those and how do you decide what goes in there and then even what you just said if you're going to launch something every week just because product the product team ships something every week does that mean the marketing team has to what do you even do send an email about it make a video yeah so I'll tell you about the five launches because we had three plans this big our work innovation some make your opinion event in London with about a thousand people in the room that was in June and so we decided to use that as a launch moment for all five because two of them were going to launch at that two were going to launch like a few weeks afterwards we were like okay this becomes the moment and we announced some of them as EA some of them as GA and so that was our launch moment so we did get up on stage we did bring our GMS on stage we did bring our design partner customers on stage to talk about their experience so we did make a big moment out of the launch but a launch never just stops there it's a rolling thunder afterwards right yeah we got the word out but now we have to actually go sell these five products and so in the back half of the year we designed our entire campaign strategy around it's like we called them the H2 plays but it's like the five plays and the five plays were all around these five products and the five products are I told you asana is a horizontal product anyone can use it but we are and the for the core product that we build all the features are great for marketing and ops teams but we also have these other teams that are in our database use it in very hacky ways and so we are just building full-fledged features for these personas. And those personas are agencies, like 20% of our customers are agencies who use Asana, and so we've picked like the client worker the time sheet budget, like just round out the full product for them, so they can execute end-to-end workflows relevant to their job. The other audience is R&D teams, like product and dev, and they've always used us in a program management capacity, but we are building out now integrating with coding agents and things like that. But when it needs a project, it can create a project in Asana. So that's the differentiation. So anyway, there's like so personal package products that we have five of these that we are building out and we launch them. So we are building out for like knowledge base and you know, and agent remediation and things like that. I'll pause. I could go. >> What's the like, so yeah, what are like that? I think people want to know, like separate from it being an Asana thing. If you cover it up the brand, like what are the like go-to-market elements of that? Is it like emails? Is it sales enablement? Is it ads? Creative? Like what's in the kind of product launch kit? >> Yeah. All of it, but where is my product? So I would say that the parts that were consistent across all five products was sales enablement. And the part in that sales enablement was it's all about the use case because we are selling workflows and to end workflows. So we have to identify the canonical 10 that all of these companies will do. And so and enable our sales team to be able to speak to it because it's a new audience they've never spoken. So like that enablement, of course, you know, your first call deck, like all of that, yes, we did demos for them to go do. But we had these use cases. >> So I like that though. It makes sense. Like it starts with let's come up with 10 specific use cases that can get everyone to understand this, train the sales team. I think it's a good forcing function. And if you have to train the sales team, that forces you to develop the 10 use cases. And then like you can't go figure out what the ads are going to be unless you figure out. >> Until you figure that out exactly. So because we were doing this at any event and many of our sales people were going to be there. They would get questions. So we first leaned into the sales enablement. So we had web pages. Like so the web pages on our website and the sales enablement were the first starting points across all of these. And then as we developed the plays, we started doing use case videos for each of these use cases that would either customer or a son or a son or just fictional of how you would do it. But a combination of use cases that are launching. We did a ton of personal content. I would say like agencies is specifically one that we are going after more actively. So just content of like blog posts I would say. But that type of like short form written content. And then the distribution mechanism was at social email the same channels. But what worked for our first go at this where we are creating most of our pipeline is because we had so many our install base. We have 170,000 paying customers that are paying and then like the free universe is even larger. We had like a install base to go to. So through our community effort, we did a lot of training. So these were like a son on tour events, which were workshops. These were trainings. And then and we are still doing them. Quick break for Zoom webinars. This is the platform behind the world famous exit five live. Someone on LinkedIn just said, I compare all other webinars against exit five live. Now, how good is that? So good. I want to print that out. Send it to my mom. Put it on my fridge. In a world of AI slot, we just want to make something that's worth showing up for. Even a webinar, especially a webinar. But don't you dare call the webinar, even though I break my own rule and do that all the time. It's a live session. Our team puts over seven hours a week into each one of these choosing the topic, the prep calls, building the run a show, and making it valuable and engaging. Zoom webinars is a big part of how we pull it off. We average 1500 plus registrants for session, hundreds of people show up live, and the chat goes off. Yeah, the last time we have a new high water market, 527 people live for an hour with us. Zoom does registration, emails, polls, analytics, and all lives in one place. So running a polished session every two weeks isn't a scramble. At Showtime, our team swears by Zoom's production studio. They preset every scene and push each one live on cue. Clean transition, zero chaos, at least that anyone can see. Just please do not look at our internal slack. Okay, all the caps lock in there. Don't share that. That's our pro level webinar production powered by Zoom. Check it out zoom.com/exit5. Learn more about Zoom and all the webinars and all their products there. And come see it live. We do these basically every week now. Go and check them out. It's called exit five live. And learn more about Zoom at zoom.com/exit5. All right, if you're at a B2B tech company spending over $50,000 a month on paid media, compound growth marketing wants to give you two free sessions to build out your 2027 plan. Free? Okay, I'm listening. What do you get? I know free is usually too good to be true. But check this out in the first session. They're going to learn your business. And in the second, they will deliver you a custom plan. So you'd know how to split demand capture and creation, which channels drive the best ROI and where you're reporting has gaps. And look, I trust them with it. I've hired CGM twice. They're one of the best agencies I've worked with back in my day as a head of marketing twice. Well, I've hired plenty of agencies as a VP of marketing and that is rare. I'm more than just a thought later, Dash. You should know that. So CGM helps high growth, cybersecurity and enterprise software companies show up earlier in the buying journey with full funnel, paid media, AEO, and a dedicated GTM engineering team. Ooh, and a former VP of marketing started it. So they actually get B2B. That's right, John was one of us back in the day. So check it out. You can go book your 2027 planning session right now at compoundgrowthmarketing.com/exit5. Link in the show notes. The goal with this is because you have such a big customer base, is it let's get our existing customers using these new features. It's not like more energy. It's not like we want to get this number of new customers because we have these new features. It's like, am I reading that right? Correct. I mean, we do want to get new customers right? Of course, our growth is always the goal. But growth will come through the new customers adopting it using it, telling people about it. And we've seen, like, word of mouth has always been such a big part of Asana's growth, like not just since I got here, but even before we have a 17 year old history, that if our customers use it and love it, AE keeps you honest. So it's like instant feedback because they know Asana. So it's like a quick iterative loop with product but also they become gaming fans, you know. So is this motion, like, because of the, Asana's like, is it one of those, like, kind of product led, but also enterprise companies where you have, you know, exactly. Yeah, we have a product led for our core product. We have a product led motion and that usually it's the graduation path once team start using. But for our we have two new products that is service management and one is, you know, just workflows, like it's called stack AI. It's an acquisition that we made. Both of those are direct to sales. So it does not have a PLG motion. It's direct to sales. And so that is the one audience where we are not mining our database. Like IT, we have to go create demand. We don't have, you know, people know Asana. But the percept, they don't perceive Asana as the product that solves the IT workflow build or problems. So we, it is a new audience with new, it's almost like positioning a new company. But with some kind of known, yeah, it's positioning. Okay. That's good. Good back. I feel that's great. That's good beginning to this. Tell me about your job. You run the marketing team. There's, you know, a hundred-ish people on the marketing team. What are, what are your big goals for marketing? How do you have the team set up? I'd love to try to like get into like your job right now, running marketing, 2026, heading into 2027. People are interested in like, who does what? How do you have the team? Are you doing weekly sprints quarterly campaign? Do you have four direct reports? Like, you know, those types of things. Can you kind of take me into like the, I guess, this would kind of be like Prachi at the, at the whiteboard, showing me the marketing strategy for the company? Yeah, I mean, our KPIs, it starts with the KPIs. Our KPIs are, we need to drive more new logo app position in our PLG machine for our four products. We need to go drive sales, five blind against all of our five products. And we need to change the brand for not just grow awareness, but change the brand perception about who was on us. So those are our primary KPIs. In the first half of this year, we did most work on the tour. And the first, like we already have a scaled engine, like how to be optimized and the third. And then in the back how we're doing walk more work on the pipe bit. So, so that's kind of like how we mapped out this year. Going into next year. That growth number one and number two become more prominent. Like that pipeline growth becomes real, we'll also make some of these products PLG. So how do you set up multi product demand gen frameworks? It's going to be top of mind for us. And then brand, you know, brand is a continued effort, but maybe that's a secondary KPI as we lean further. It meets up brand takes yours. But we had a lot of work on that upfront in terms of team organization. We have two demand, gen demand creation teams. I have a growth marketing team whose primary KPI is that PLG new local acquisition or trials. And then we have a revenue marketing team whose primary KPI is pipeline for sales. Now both of these teams are tied to the hip because there's a lot of digital digital channel. Then we do campaigns that has cross over. So they have to be like what team in many ways, but they have two separate teams with different KPIs. And then I have a product marketing team, I have a brand and creative team, I have a comms team, and a lofts team. So the rest of the team stock is pretty standard. - Okay, I'll come back to, well, wanna come back to NSAC on the, so the growth, you have the revenue and growth. Do they have shared resources or do they each like running their own ads as an example, and they share learning? - No, so I've done it. - So Chackle was also a PMG NSLG company, so I've done it. - I'm asking this question 'cause every, so many people that listen to this one, and there's like a lot here, like a lot of, this comes up a lot, which is like, hey, we got, we got a sell to the enterprise, but we also have the self-serve thing. How do we work together? 'Cause it's not perfect. Tell me, yeah, tell me about what you're doing. - I'll tell you what we're doing at the salon, then I'll also reference my Chackle, how I had it designed at Chackle because I think the scale matters. So here, they have their primary KPIs, and they have dependency on each other's KPIs. Like we need campaigns to also drive some trials, we need digital channels to drive pipeline as we do. And so there's like our demand model has that, but they are the DRI, and so they have to work with the cross-functional team. So let's say like on makeup, this is not true, but like let's say in Germany, like our pipeline is down, and paid search and not bringing anything, if that were a problem statement. Then the DRIs might have a new marketing leader, but they would work with the digital team to figure out what is happening with the budget go down. So they pull in the team to make a decision. - Where is the digital team part of the revenue? - Digital is part of growth. - Oh, got it, okay. - Growth marketing has life cycle, education, so like expansion, but also digital acquisition, which is, you know, where SEO-- - That's the high volume, like-- - Big media, all the high volume channels. And so that is how we've structured it at Asana because our paid and web channels are very scaled. And if I start doing, if I start replicating efforts, it's gonna be inefficient for us. As a team, I'd rather give them primary KPIs and hold them accountable. And we have operating cadences that help us do that. At Chakur, we did have a small portion of SMG budget that we ran through an agency that our revenue marketing leader did own. The subject matter experts from the growth team weighed in on the strategy with this agency, but they manage the agency themselves to kind of drive because it was like segmented in that way. Like Chakur was SMB was largely self-self and enterprise was largely revenue. Here, anyone can come in through growth. So it's like, just, it's different in that way. - Have you learned anything about the KPIs and incentives that matter here to foster the right relationships between the teams versus, I don't have as much experience. It's just a very one small example. Maybe this is just my outlier example, but it felt like when you silo the teams, they're very like, nope, this is my job. My job is to generate MQLs in this segment. And as long as I do that, I'm gonna get my bonus and I'm gonna do my job. And it's like, well, no, we should, we could be helping this team. Like, have you learned anything about how to get everybody kind of rowing together, even though we have different goals? Or do they have, do they have different goals? - Yeah, so the metrics matter. So their primary KPIs is the driving function for how they think what programs they put, what strategies. But one of the things that I've always done is when you start over here and you do your demand model of like, hey, where is this demand gonna come from? I have carved out demand models by channel. So it's not just enough to say, okay, we have like a $x million pipeline goal. We take it down to like, where we believe what channel is gonna drive that? And so then have the, let's say web market or carry the goal, secondary goal of pipeline in addition to the trial. And so one way to do that would be, okay, I might need to change my top of funnel mix to bring in more ICP, that's converting, like this. So that's one, not ideal, but it does help to give them a secondary KPIA that they know is like on their channel, they're tracking. And then operating cadence is matter also. It's like, so when we are running like funnel reviews for pipeline, we do invite outro leads, especially like paid media, which is driving or, you know, web to weigh in and listen to the sales and feed back so they can take it back. So they have accountability because they're on the call versus the accountability is not connected in that way just behind the key leader who owns it. So that's my way of doing it. Like in an ideal world, you could say like, hey, put both of these under one leader. It'll do, we definitely don't want to create inefficiencies, but that's a lot of like hierarchy. Then I am that leader, like I can figure it out. I mean, I have four other things, but at some point maybe we need to create that hierarchy. Like, but right now it feels like, okay, these two leaders can work together. Like we are part of one team. So that's how I've solved it. - All right, tell me, how do you run the team? So you, you're a member of the exact team as a CMO. You all have your off-site somewhere. You come up with these three key KPIs for the year. Now, Prachi has to take these back to her team and then actually go and like make the bets and plan the strategy. Can you take me into like the team KPIs and then also just like how, what does your team look like? You have 120 people on the team. They can't all report to you. Seems like you're very involved. Who reports to you? What is your direct reports like? What do you expect out of them? What is your operating cadence? People love that stuff. I'd love to get some of that from you. - Let's take on your planning because we are into it. My play, I have a playbook for that and I think it works well. So my playbook is usually like these off-sites. We have enough warning that that off-site is coming, which is exact off-site. I love to do like a marketing leaders off-site or like session before that. To like hash through like what did we learn this year? What would we do differently? We all have a general sense of what I have a sense of what our primary KPIs might be. It might change a little bit as we do this off-site but where don't we head in? And so we do a little bit of high-level brainstorming so I take some of that thinking into my off-site and sometimes I'll have a deep dive topic or not but we work on that. And then so what that generates is like more of a top's down direction of like your other primary KPIs. Here's what our job is. And I have some input on what's worked or not worked from the team directly. And then once that off-site is done, then we do a full bottoms of build to say, okay, these are our top line KPIs. But we know, usually we know what our resourcing is. Let's do a bottoms up to say, what is it gonna take to hit those goals? If you need more resources, why? Usually we'll do a lot of debating with our own teams where we invest in. So we do what we do at top's down. We do a bottoms up. There's always a gap. It's like never happen that you have a top's down in the bottoms up like matches. And then it's like a negotiation. A negotiation with finance, sometimes negotiation with sales, sometimes to be like, okay, we can do this with this resourcing finances and know what else can outbound take. Or something like that. It's negotiation. - Are you in the thick of this? Are you in the thick of this now for next year? - Yeah, we kicked off planning. So we are doing this right now. And once like that, the negotiation happens and we generally have a sense of like, okay, what is our envelope? What is our resourcing, what are our goals? Then we go and lay out plans. And like, I used to do quarterly planning only. And we like, okay, we like, we have a general sense of what quarter, but like really get the quarter, right? I've moved more recently more towards like a six month plan. We just have more detail into future because it was just becoming too, we are spending more time in planning. We days, so I've like stretched that out to six months, but I don't go beyond six months. Like we generally know like, oh, we have this big event or like those things we know, which we have to pre commit to. But outside of that, like we haven't decided exactly what campaign the theme is. And right now with the piece of innovation, we have to be nimble. Like being a small team doesn't matter. Like you have to be so nimble as a marketing team. So that's my framework. And then in terms of cadences, it's pretty standard. Like we do weekly marketing calls, where we do a dashboard review. Like the leaders talk about what's top of mind, what's working, we do MBAs, which is like monthly business reviews that are more deeper diving to insights. And especially focused on if something's not working, what are we going to do? What is the action plan? And then we have QBRs at the company level. We also do marketing QBRs, especially for larger teams, because it gives me an opportunity to cure from the teams. So it's a pretty standard cadence. So we do that. - What would be like a topic in a NBR? Like what are you reviewing? All of marketing, parts of marketing, and the same question for the QBR. And then who's the audience for those? - Yeah, so QBR, I'll start with the QBR. QBR is often functional. And so we look at the goals for the function, it's like a recap of the quarter and like a big priorities for the future quarter. - You have to get up in front of the company and say, "Hey, we said we're going to do this this year. Here's how we're pacing towards that and here's what's going on." - So we don't do that at a SANA level. So marketing is not presenting a QBR to the rest of the ELT, but my individual leaders are doing a roll-up. And for SANA, we do weekly goal updates, and then we do have goal reviews every month. And then we do what we call an QBR, which are like strategy sessions every quarter. So but our QBR is just for me to roll up what's happening in the business and what are our key priorities for Q2 or like future quarters. And then the monthly is more deep dive into very specific things that we are seeing that are read or sometimes they are very green, like what more can we do? But it's mostly like if something's very red, like so it's not like every function, every metric, we do a high level metric review, but it's like really focused on like, hey, I really want to discuss like enterprise dimension or what have like one key narrow agency campaign or what that is top of my for me or the exact word or is read. All needs a ton of alignment and I just don't see it. So it's like we pick those topics, TBD, and then VK is a dashboard review with pile of all insight. - What is your direct report structure look like? - I have rev marketing, growth marketing, brand and creative comes product marketing marketing ops. didn't do all spend time separate from the team like with your leadership team. Yeah, yeah. Quarterly offside, running offside. We have a weekly M&T call. I do one-on-ones with each one of them. So yeah. How do you keep things nimble, but also at the same time not like burn out the team? I feel like a lot of time one of the sentiments that I'm feeling right now in marketing is like because things do change so much like that is awesome. I hear you. We've got to be nimble. But I've also seen like when you whip lash and change too much, everyone's like it's hard to keep morale high when you're doing that even though innovation is happening. Yeah, so it's not something that we've solved, especially with the pace that is happening right now. So I don't want to act like, oh, I have the perfect playbook. I think the things that are working for us, like on okay, I'll say two things. One is I do think like the six-month planning forces to pick the biggest bets that we'd want to do anyway and gives us enough insight into what's coming in the next few months that we can drop if we need to pick something else up. So I think that forces quarterly planning that the longer runway does help with that. I think the second thing is over-emphasizing on just like context communication and clarity. Like I've always done it as a leader, but I'm doing that so much more now on in terms of like getting the team to because sometimes they might foresee something that needs to change. That we'll, if I hadn't done that, would come later as a like, oh, we got to go change this. And so that is another aspect that we are really trying to give a lot more clarity. And like that was some of the feedback from the team. It's like the monthly all-hands feels like not enough. So let's do something weekly. So async calls, by the way, we've done a bunch of things, but so communication and transparency and context across the war is the second thing. And I think the third thing that is helping is clear roles, very, very clear roles and accountability and a decision-making framework. So when something comes and you have to move fast, I want to the extent possible. I want every person to know, can I make this decision myself? Do I need somebody else involved? When do I go to my boss? When do I go to Trachi? When do I go to a CEO? And so we've really tried to, we use this framework called Rad for decision-making. And we are really trying to like create like that clarity for every team, every project. And again, it's not perfect, right? This is work in progress. But I think those types of things are helping us and our team. Is that like a role specific? Would I have a framework or is it like team specific? How do I know when to deploy that that decision-making framework? Rad, we want to use it. It's like who's responsible? Who has to agree and who's the final decision-maker? So that's like Rad. And we we try to use the same framework across every, every single project. And I don't want to see, you know, agree you can have multiple names. But in R&D, I only want to see one name. And then when we move the project, like we get that alignment across the work to say, like, hey, this is my Rad, especially for bigger projects, smaller projects, generally the team knows what has to come to me or you know. And so that helps with, we saw some of this, especially when we were working through our product launches. It's like not having that rad defined early on. We created some rework because all like we needed the CPO, but sometimes you need to get the CEO. And it's like we, that was very avoidable. Like we could have gotten ahead of that with a framework. That's when we implemented it. So it seems to be working better now. But like this is going to test all of us as marketers. Like we, so yeah, I know I mostly was asking not because I think you'd have a perfect answer. But I kind of wanted to like say it out loud because I do think everyone listening to this is kind of navigating this. Yes. In real time. Yeah. Okay. I want to wrap with one question I didn't ask you about, which I wanted to get to is so you did this whole rebrand and not not a rebrand repositioning is probably the proper thing. And in this doc famously did not hire an agency or a positioning consultant to do this. Why you did this all in house. Tell me why and does that say anything about the future of working with agencies or was this just a thing that you needed to get done in house. Take me into that. Yeah. I mean, I have done positioning three or four times in the last 10 years. And I've used an agency for every one of them. Like the agency or contact like somewhat like an expert for every single one of them. And I would have used one here as well. In fact, I did talk to the top three that I thought would talk three. And we did talk about the project got, you know, really went deeper. The biggest constraint why we didn't go with an agency was we had the time was not on our side. Like this entire repositioning and rebrand had to be done in 90 days, which meant like I needed a partner who could work at our pace. But I didn't know we have so many executives involved like schedules like all of this stuff was just going to like throw timelines off. And like the proposals I got even if the personas we brought in were the kind of people who would work in our pace. They just didn't have the bandwidth or like the timelines were delayed. And so that was the forcing function to take a step back and say, okay, looks like I'm not going to be able to bring an agency here. Then what is my what is my path forward? What helped me here? Like you what is the biggest value problem bringing an agency is either experts would be you have like a sounding word someone who you can work with on these these things, you know, someone who's bringing a fresh outside and perspective. Otherwise, you get kind of you get in your own world. And it's it can be more inside out. For me, I was new. So that I had the outside and perspective. But two is our CEO comes up from the marketing path. So he was in a established CMO like right? He's now CEO like multiple times CEO, but he has that background. And so having him as a thought partner works really well. And like that was out alignment. Like hey, I'm going to reach out to you more times than I would typically, but I need that thought partnership. So that kind of worked out. Oh, okay. I should have asked Dan Rogers. I interviewed him back in the day. He was the CMO at service now. I feel like yeah. Okay. He's a really good marketer. Why? Yeah. Yeah. So it helped having him as a sounding board. And that helped move the product. I mean, and the positioning exercise really is like a company strategy exercise, too. The so the CEO has to be involved. If not lead it, but those two were like my drivers for why I didn't bring in an expert. Yeah. That's that's like a hugely positive thing. Then if you believe if like the CEO gets marketing has done this before that, that is your agency is kind of you in the CEO working on this and rolling it out to the team. Yeah. I mean, you have to carve out time, right? Like that's hard, but we were both new-ish. And so it kind of helps. Okay. You don't have to answer this question, but I'm going to ask it. I'll be I would be you mentioned like the top three. Are you able to tell me who the people you may have considered? Because everyone's going to ask like who should I use for positioning? Are you do you want to give any names? You can pass. It's okay. No pressure. Well, I'll tell you who I think got amazing. And then these may already not be the exact ones I should do, but I work with April done for in the past. And so I've done with her fire breaks was one that I've met a couple times has been recommended. So I like Bob and fire breaks. And then Andy Cunningham is another one who I was introduced to at great conversations with. So there were a few. I met quite a few of them, but what about this guy called Claude? I heard he's great. Claude, I think with excellent prompting and a lot of like your own POV inserted, Claude can be a great brainstorm partner for sure. And one of the things like I told you I created my brand strategy just agent are back up. You know, the we use that agent uses Claude, but I fed it frameworks that I believe for positioning books that I had and I gave it very detailed like an exercise of how I would do this. And then it became a pretty good brainstorm partner. So I would give it credit, but it's a lot of generic words that the aha has to come from you. It's all about the workflow. Now, once we got that, we were able to use that. I'll give you one just personal story related to that. So we had our big event in September. And I needed to do the welcome, like the keynote, right? And I love writing, creating public speaking. Like I would tell you that that's my thing. Yeah. But I could not get going on my talk. Like I just, and that's never happened. Like since I got good at this stuff, like 10 years ago. And I was like, oh my God, did I like, did AI like ruin my brain? Like am I not allowed to have, and am I not able to have an original thought of my own, right? And a friend of mine was like helping me on it. This guy Harry dry. He's an amazing storyteller and writer. He runs this website called marking examples.com. And he's like, dude, put, he's like put away the AI, put it away. Like just, just what does Dave Gerhard think? Like what do you think? And I think that was such an important lesson because it's like that is the unique thing. So for like you and Dan Rogers to have your own gut feeling, that's like what makes it good. It's like, you know, the homemade meal is what's going to make it unique. And I was such it important lesson. And I'm like, okay, the AI stuff is awesome. There's a lot of like interesting things like. And it works. You know, when we use the AI, it's like, I love seeing, and then does everything in situ. So we would like just feed it in cloud and be like, show me the whole page. Awesome. We could move so fast because it's like this works. This doesn't work. But anyway, I've used cloud and all of the elements a lot. So I don't want to like, but there are some things which I feel like start with. Yeah. Well, you don't want to say anything because there's cloud, cloud is like, they're going to run the world. And so you don't want to put anything into it. And it's a reuse. It's a ton. So there's a lot of stuff that cloud can do and do well. But some things just require human creativity, input, or cloud. Okay. Last question. Give me a name of one CMO that I should have on this podcast that now that you've spent an hour talking to me and hanging out, someone who's awesome, appear of yours that you think I'm not asking you to do the outreach. I'll do it, but who should I get? Wow. Okay. I love Amanda Blue Beach CEO like she is. Oh, I don't know. Okay. Okay. Send you a link but she's blue beach, but she is amazing. I think she do great on the phone. Okay. That's the right. Prachi, thank you so much for coming on the podcast. You did, you did great. It was great to hear from you. I hope that you get at least one new LinkedIn message and connection after this podcast. You'll get a bunch. Great. I'm really free all this time. Thanks for coming on the podcast. It's been great to have you. Thank you. I enjoyed this. Thanks Dave. Okay. I'll see you later. Okay. Bye. Hey, real quick before we wrap up, I just want to give a quick shout out to all the stuff that we're doing at exit five.com. You can get on our newsletter there. A couple times a week we're going to send you some really useful stuff about B2B marketing. Our whole mission is to help you get smarter about B2B marketing and get better at your job. In a world where everyone is talking to AI and Claude about how to do marketing, our whole pitch with exit five is real insights from real people. We've built our whole business around it. You hear it here on the podcast. Just see it in our newsletter. And check out all of our stuff. We are creating the number one resource for you B2B marketers. So go and check it out exit five.com. Get on our newsletter. You'll find all of our podcast links there. Show notes, all of our webinars, articles and a bunch of other stuff. Plus you can also join our community over there. So check it out exit five.com. The best marketing leaders have a strong agency or two backing them up and convertive is one I put on that list, especially if AEO is a priority for you right now. It definitely is and a good one is a lifesaver. They bring fresh creative angles and go deep on specialties like AEO when your team's short on bandwidth. They're shopping for a B2B agency. Check out convertive. They help enterprise marketing and opts leaders grow revenue across the business. Who do they work with? They work with legit companies like docusign, data bank and constructor. And they build on the search work that you're already doing optimizing your site. So more buyers find you and turn it into pipeline. And this month exit five listeners get a free AEO search snapshot. They'll run your buyers real questions through Google and AI tools. Show how you stack up against competitors and tell you what's worth fixing. So if you're building your AEO strategy for 2027 start here. Go and check out convertive.com/exit five. That's convertive.com/exit five and you can see the link in the show notes.

Podcast Summary

Key Points:

  1. Mcheal from Optimizedly won an AI agent showcase by building 2000 custom landing pages using signals like job postings and press releases, showcasing AI’s power in ABM.
  2. Optimizedly’s AI agent platform enables B2B marketers to build or use 50+ prebuilt agents to automate tasks, join meetings, and support campaigns, turning websites into dynamic tools.
  3. Webflow helps brands become revenue drivers by enabling AI-powered content creation, campaign generation, and full customization without developers, launching new "Webflow Campaign Agents" to streamline workflows.
  4. Prachi Gauray, CMO at Asana, repositioned the company in six months without hiring an agency, focusing on internal creativity, CEO alignment, and clear decision-making frameworks.
  5. Asana shifted from a project management product to a “work execution” system by integrating AI agents into workflows, improving team efficiency and enabling shared memory across stakeholders.
  6. Asana launched five new products in six months, using a single event launch moment to drive awareness and then rolling out campaigns focused on key use cases.
  7. The marketing team at Asana is structured around demand-gen, growth, and revenue marketing with clear KPIs, operating cadences, and cross-functional collaboration to drive pipeline and trial growth.
  8. Human creativity and leadership insight remain irreplaceable—even with AI tools—highlighting that personal judgment and strategic alignment are essential in modern marketing leadership.

Summary:

This episode highlights how AI is transforming B2B marketing, from automating workflows to redefining product positioning. Mcheal from Optimizedly demonstrates the power of AI agents in ABM by building thousands of custom landing pages from real-world signals, validating AI’s potential for targeted marketing. Optimizedly’s platform empowers marketers with AI agents that can join meetings, manage campaigns, and maintain websites—making AI a core part of daily operations.

Similarly, Webflow enables brands to leverage AI for content creation and campaign automation, turning websites into ongoing revenue engines. The conversation with Prachi Gauray, CMO at Asana, reveals how a strategic repositioning—without external agencies—was achieved through internal alignment, clear decision-making frameworks, and CEO involvement. Asana shifted from project management to work execution by integrating AI agents into workflows, enabling teams to collaborate more efficiently and build shared memory across functions.

Five new products were launched in six months, using a high-impact event as a launch moment and building campaigns around specific use cases. The marketing team is structured with clear KPIs and cadences, emphasizing collaboration between demand, growth, and revenue marketing. Ultimately, the episode underscores that while AI enhances efficiency, human creativity, strategic leadership, and real-world experience remain essential—proving that the future of marketing lies in human-AI synergy, not automation alone.

FAQs

Optimizedly's AI agent platform helps B2B marketers build custom AI agents or use pre-built ones to automate tasks like content creation, campaign management, and meeting follow-ups. It supports virtual teammates that learn over time and can join meetings, generate content, and support marketing campaigns.

Optimizedly uses signals such as job postings, press releases, and leadership changes to identify and target specific decision-makers in ABM campaigns. This enables highly personalized outreach and improves targeting accuracy in B2B marketing efforts.

Virtual teammates are AI-powered digital agents that learn over time. They can join meetings, complete tasks, support marketing campaigns, and keep your website updated, acting as proactive, intelligent team members in your marketing workflow.

Webflow helps marketers build fully custom websites without developers and integrates AI agents to generate campaign briefs, on-brand landing pages, and matching ads—making it a powerful tool for turning websites into AI-powered revenue drivers.

Asana repositioned itself from a project management tool to a work execution platform by integrating AI agents that collaborate with humans. This allows for automated workflows, such as creating content briefs and action plans, reducing manual effort and improving team efficiency.

The primary KPIs include driving new logo acquisitions through product-led growth, increasing sales pipeline across five new products, and changing brand perception to reflect Asana’s shift toward work execution via AI and agents.

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